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<h1><a href="https://archiveofourown.org/works/28256715">Cherry Pie</a> by <a class='authorlink' href='https://archiveofourown.org/users/AshwinMeird/pseuds/AshwinMeird'>AshwinMeird</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>5 + 1 Things, Alive Mary, Alternate Universe, Christmas Fluff, College | University Student Castiel (Supernatural), College | University Student Dean Winchester, Engagement, Established Castiel/Dean Winchester, Everyone else knows, Fluff, Funny, Good Parent John, Good Parent Mary, Happy Ending, High School Student Sam Winchester, Home for Christmas, M/M, No Homophobia, Oblivious Sam Winchester, POV Sam Winchester, Sam Finds Out, Secret Relationship, not really - Freeform, shipper Mary</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-23</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-23</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-10 19:40:48</td></tr>

<tr><td><b>Rating:</b></td><td>Teen And Up Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>3,495</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/28256715</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/AshwinMeird/pseuds/AshwinMeird</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Sam Winchester's older brother Dean left for University three years ago.  Now all his parents and Dean can talk about is this new friend of Dean's: Cas, but Sam doesn't quite understand what sets this friendship apart from the others Dean has had.</p>
<p>or</p>
<p>Five times Sam thought Dean and Cas were friends and one time he finally figures it out.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester, John Winchester/Mary Winchester, Sarah Blake/Sam Winchester (minor)</td></tr>

<tr><td><b>Comments:</b></td><td>10</td></tr>

<tr><td><b>Kudos:</b></td><td>249</td></tr>

</table>

<a name="section0001"><h2>Cherry Pie</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>This is the closest thing I'll be writing to a Christmas fic lol.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  <b>1</b>
</p>
<p>Sam and Dean had always been very close, closer than a lot of brothers, they texted each other all of the time and called most nights; which is why Sam was surprised to hear about Dean’s new friend through their mother.</p>
<p>Not that he has against Dean telling their mom anything, just that Sam was always told first when it came to stuff like this.</p>
<p>Plus Mary tended to be a bit much when it came to little things sometimes.</p>
<p>Sam had come home from school one afternoon on the bus when he walked in on his mom excitedly telling someone that she loved them through the phone.  Sam knew this meant that Dean was on the other end, most likely trying to end the conversation for not the first time, because he was in his third year of University a couple of hours away and all of Mary’s calls with him ended this way.</p>
<p>Once she had finally put the phone down, Sam’s mom just continued to grin widely into it like the phone was a winning lottery ticket.</p>
<p>She hadn’t even noticed Sam enter when he finally tapped her on the shoulder.  His mom’s grin faltered for a moment as her gaze jumped to her youngest, but it quickly returned.  “Hey,”  He greeted, “What’s up with Dean that’s got you all happy?”</p>
<p>She smiled broader, if that was possible, before answering, “Dean’s finally met someone.  His name is Castiel, but Dean calls him Cas.”</p>
<p>Sam gave his mother an odd look.  Surely she knew that that phrasing was used when you meet someone in the <i>romantic</i> sense?</p>
<p>“Okay,”  He said after a moment, “Good for him I guess.”</p>
<p>Mary nodded her agreement.  “Dean says they met over summer break, but I suppose I don’t really blame him, after Michael and all.”</p>
<p>Sam remembered Michael; nicknamed ‘Mikey’ by his brother.  He and Dean had become close friends back in their last year of high school, but Sam never really liked him because Sam was fourteen and convinced he should have the monopoly on Dean’s free time.  They went everywhere together for about four or five months, Michael had even become close with John and Mary, until one day something happened between Dean and him and suddenly everyone acted as if Michael had never even existed.</p>
<p>He had tried to ask his parents about it in the past but any time he got close they shut him down.</p>
<p>Sam wondered what made his friendship with Michael, or this Cas guy, different from Dean’s friendships with Garth, Jo, or any of the guys in his grade back in high school.</p>
<p>Before Sam could ask about anything related to this or any of Dean’s other friendships, his mom happily got up from the table and started to throw some dinner together.</p>
<p>Sam decided to just let her be happy for Dean making a new friend like he was some kindergartener for the rest of the night, even after she made his dad smile with this ‘amazing’ news.</p>
<p>
  <b>2</b>
</p>
<p>His mom had first told Sam about Dean’s new friend back in October, the following two months made ‘Cas’ a commonality in the Winchesters’ vocabulary.  Dean couldn’t go half a phone call without bringing up his friend, his mom would recount the stories Dean had told her to Aunt Ellen, and he’d even heard his dad and Bobby talking about him one Sunday dinner.</p>
<p>They were best friends.</p>
<p>Dean and Cas were such good friends, in fact, that when Sam asked his mother why the pie he was bringing for his night at Dean’s apartment was cherry and not apple, Dean’s favorite, she said it was Cas’.</p>
<p>Sam was going to Dean’s apartment for the first time since he had visited over summer break, both he and his brother were quite busy with school and Dean did live over five hours away, so they didn’t see each other in person too often.</p>
<p>But now it was Christmas break, Sam was done after Dean but his brother technically was still in school until he wrote his exam on the 21st.  So Sam was driving up to meet him after he was out for break and the two were following each other home the day after Dean’s exam.</p>
<p>Sam had gotten his full license eleven months prior and this was the first time their parents were letting him drive on his own, but he made it there alive and was now walking up to the small apartment Dean lived in.</p>
<p>He had the bagged pie in one hand and his backpack across his shoulder.  Sam was about to buzz up to his brother’s room when a short redhead interrupted him by stepping out of the door.  “What brings you to our humble abode today, Mr Sasquatch?”  The girl asked excitedly.</p>
<p>“I’m- uh, just here to visit my brother,”  Sam said, trying not to lean too far away from the intimidating girl.</p>
<p>“And what, pray tell,”  She began, “Is your name good sir?”</p>
<p>Sam could tell the girl was fucking with him based on the barely concealed smirk adorning her face; he decided to play along.  “They do call me Winchester, Sam Winchester.  And you milady?”</p>
<p> The girl took a step backwards to look up at him quizzically.  “As in Dean’s little brother?”  She asked in an uncertain voice.  After Sam’s nod she continued with an outstretched hand, “I’m Charlie Bradbury, his best friend.”</p>
<p>Sam shook her proffered hand, but before he could ask any follow up questions a soft ringing filled the air between them.  Charlie stuck her hand in the bag covered in multi-colored pins and took out a ringing phone.</p>
<p>“I’m sorry, my girlfriend is here to pick me up.”  She stepped out of the door but held it open for Sam.  “It was nice to meet you, say ‘hi’ to Dean for me.”</p>
<p>Charlie answered the phone call and was beginning to explain her run-in with Sam as she briskly walked down the steps and out of Sam’s hearing range.</p>
<p>He turned towards the inside of the building and made his way into the lobby.  One thing was bothering him though; why did Charlie say she was Dean’s best friend?  Could someone have multiple of them despite what the title implies?</p>
<p>On the other hand, Charlie said she had a girlfriend, and not in the female amigo sort of way.  Sam didn’t even know Dean knew anyone in the LGBT+ community, but then again their home town wasn’t exactly the most prideful place on Earth.</p>
<p>
  <b>3</b>
</p>
<p>Dean’s apartment was on the third floor of the building, number 306.  When Sam finally trudged up all of the stairs, because Dean said it was faster than the elevator, and knocked he was confused for a moment about why there was a burly college aged dude answering and not his brother.</p>
<p>Then he remembered.  “Your Dean’s roommate, Benny, right?”  He asked the man in front of him.</p>
<p>He nodded.  “And who’re you?”  Asked Benny with the southern accent Sam had heard in the background of a couple of he and Dean’s phone conversations.</p>
<p>“I’m Sam, his brother.  He said I was supposed to come today, right?”  Sam asked, knowing perfectly well that Dean would be the person to forget to tell his roommate about a visitor staging over.</p>
<p>Benny nodded and moved to let Sam in the room.  “Yer brother should be home at about six, it’s his last exam tonight.  So we should be eating around seven, but if you get hungry feel free to take whatever.”</p>
<p>“No problem,”  Sam said idly, wondering what he’d be doing to kill forty five minutes until Dean got home.</p>
<p>“Sorry ‘bout not bein’ too hospitable, but I got a test t’study for so I’ll be in my room for most of the next twenty four hours.”</p>
<p>Sam looked over to Dean’s roommate.  “Dude, it’s okay.  I can just chill out here,”  Sam indicated the kitchen-living room area, “For a little while.  I don’t need a babysitter.”</p>
<p>Benny looked relieved.  “If ya need anythin’ just holler.”  He started to step towards his own room before looking at the door to Dean’s, “I’d also recommend not going in yer brother’s room, and if you have to, don’t touch anythin’.  Lord knows what he and Cas get up to in there.”</p>
<p>Sam snorted, before agreeing, “Yeah, that’s not something I plan to do,”  Before Benny retreated the last few steps and shut the door to his own bedroom.</p>
<p>Sam laughed to himself, knowing how anal Dean was at home about people entering his holy ground without explicit permission.  He wondered what kind of lecture Benny must have gotten about Dean’s hatred of anyone invading his personal space or, god forbid, touching something of his.</p>
<p>Dean’s room at home was a no enter zone, so Sam hadn’t expected his apartment room to be much different.  But Cas, according to Benny at least, was allowed inside.</p>
<p>His brother really let this dude he’s only known for like five months, at most, in; how special was this dude?</p>
<p>
  <b>4</b>
</p>
<p>True to his word, Sam is quiet as a mouse while waiting for Dean to get back to his apartment.  But there’s one problem.</p>
<p>Mice have <i>boring</i> lives.</p>
<p>He’s already cycled through the four apps he keeps on his phone and opened all of the nine million stories that people on his Snapchat feel obligated to upload.  Now he’s just staring at the popcorn ceiling and hoping that Dean will be finished of something early for once in his freaking life.</p>
<p>Sam lets his head drop to the side and notices the frame covered shelf above the TV.</p>
<p>Where there’s frames, there must be pictures.</p>
<p>At this point nothing could make him more bored, hopefully, so he dragged himself off of the couch and stood by the shelf.</p>
<p>Over half of the photos were of Benny, some with older people and some with people his and Dean’s age.  Several of the photos were of Dean, Charlie ,and several other people (in pairings of larger group photos) dressed in old fashion clothing and a majority of the people seemed to be holding fake swords.</p>
<p>Sam made a mental note to ask Dean about that one later.</p>
<p>The last few were of Dean with various friends and family, Sam only made it once which he was not annoyed about.  Not at all.  But there was one that stood out.</p>
<p>In real life, and all of the photos in front of Sam, Dean wasn’t a touchy person.  He was the type to give you a side hug or maybe a really fast squeeze if he hasn’t seen you in a really long time; he was no different in photos, in most he was just awkwardly leaning against someone else or just wholly not even pretending to be touching them.</p>
<p>But this one photo...  The one with the dark haired dude that Sam didn’t recognize...  This person, who Sam could only believe to be Cas, was full on hugging Dean from behind.  It was taken in the kitchen of this very apartment; Cas was standing behind Dean, who was cooking something, with his arms around Dean’s waist and chin hooked over his shoulder.</p>
<p>They were laughing at something and Dean appeared to be fully leaning back into Cas.  Sam could only assume that touching like this happened regularly between them; Cas was probably just a touchy person.  It was probably a good thing for Dean, Sam thought, that his brother was getting physical contact like a normal human being now.</p>
<p>He would have analyzed the photo deeper, except, the sound of a key in Dean’s door snapped him out of his trance so he (gently) placed the photo back on the shelf and vaulted the coffee table to be laying on the couch when his brother finally opened the door.</p>
<p>
  <b>5</b>
</p>
<p>His night with Dean, and Benny while he ate with them, was awesome.  He and his brother ordered in Chinese food from the place across town even though Dean insisted he could actually cook unlike their parents.  And the two of them went to glow in the dark mini golf before retiring in Dean’s apartment for the night.</p>
<p>They mostly hung around and ate pie the whole time.  Their mom had learned over the years that no matter the size, Dean would eat the whole pie, so she just bought smaller tins.  Because of this Dean ate half the pie in two slices, Sam had a quarter in one slice, and the final slice was surreptitiously placed into the fridge.</p>
<p>Dean Freaking Winchester placed a piece pie in the fridge and proceeded to take a bag of chips out from the cupboard because he was <i>hungry</i>.  What had Cas don’t to him.</p>
<p>The following morning had the two waking up earlier than Sam would have liked on his second official day of Winter Break, because whatever happened on his last day in class was certainly not educational.</p>
<p>They had bacon for breakfast.  No seriously, that’s all they ate, something about not bothering to get more groceries because Benny was leaving the day after them anyways.</p>
<p>After that Dean drove Sam to the mall for some last minute presents and just acting childish in public at all of the dumb things they found along the way.</p>
<p>They ate at the mall before heading back to Dean’s apartment, by then it was almost one and they had decided they wanted to be on the road before one thirty in order to make it back home before a late dinner.</p>
<p>Sam packed his stuff back into his bag easily and Dean already had his stuff waiting to be put in the Impala, but was making no move to actually leave the apartment.  Dean was typing away on his phone, completely oblivious to the confused look Sam was sending his way.</p>
<p>After several minutes of silence, Sam finally asked, “We heading out anytime soon?”</p>
<p>Dean finally looked up from his phone, somewhat startled, before he shook his head.  “Cas’ll be here soon,”  He said, staring into his phone again.</p>
<p>To Sam’s utmost shock, he realized that this was the first time he’s actually heard Dean mention Cas since he arrived yesterday.  Maybe the two weren’t as close as Sam thought they were, or, based on the open ended sentences and topic changes Sam noted, Dean had purposefully not said anything.</p>
<p>Instead of asking or arguing with his brother, Sam merely nodded and the two went back to silence.</p>
<p>Cas arrived about ten minutes later.</p>
<p>Despite having heard about the man constantly, Sam was not prepared for him.  Cas was almost as tall as Dean, which was slightly taller than Sam still even though everyone says he’ll be taller than Dean eventually.  </p>
<p>Other than their height, Cas shared little in common with Dean from what Sam could tell.  He wore an honest-to-god trench coat, spoke like someone handed him a thesaurus and told him to have at it, and he seemed to be lacking a sense of humor completely.</p>
<p>That is until Dean started laughing at something Cas said and Sam realized he was being sarcastic and dry intentionally.</p>
<p>Sam and Cas got along great, which is why Sam was so surprised when Dean looked at the time and suggested that Sam get on the road.  Despite it actually being their agreed time of departure Sam argued, “Why, you’re not leaving yet?”</p>
<p>Dean rolled his eyes.  “And you drive slower than I do,”  He gave Sam a critical look, “At least you should.  And Cas here needs to eat his piece of pie.”</p>
<p>“Okay, I’ll go,”  Sam agreed, knowing Dean was going to be home that evening no matter what, “I’ll tell Mom and Dad you were a little behind me, but I’m not covering for you if you miss dinner.”</p>
<p>“I won’t Bitch,”  Dean said as Sam got up from the couch.</p>
<p>“Jerk,”  Sam retorted, before turning to Cas to say his goodbyes.  His brain decided to ignore the odd looks Dean and Cas were giving him for this because it had already entered drivers mode.  “The pie’s cherry too, Mom said it was your favorite,” Were Sam’s parting words as he turned to leave.</p>
<p>As he shut the door he heard Cas say, “Pie isn’t the only thing that cherry is my favorite of.”</p>
<p>Sam thought about this for a second before internally disagreeing.  Most cherry things were actually ‘cherry’ flavored, and Sam wasn’t really a fan of the natural or artificial flavoring.  If he had to choose a flavor of something like Kool-Aid or lollipops, he’d most likely choose grape.</p>
<p>
  <b>+1</b>
</p>
<p>Sam wasn’t one to use his phone while driving, except for that phone call from his mother that he just had to put on speaker to take, so he had a text from Dean saying that he left about forty five minutes after Sam did.</p>
<p>Damn how long did it take Cas to eat a piece of pie, with Dean’s help most likely?</p>
<p>Either way, Dean drove considerably faster than Sam and would easily make up any lost time that way.  Which is why Sam was not surprised to hear the Impala in the yard after barely making it into the kitchen himself.</p>
<p>Mary, who had been grilling Sam about every second of his drive home, suddenly perked up at the sound of Dean’s car vibrating through the whole house.  She had left the kitchen before his dad migrated in from the living room with a small smile on his face.</p>
<p>Yes, Sam did understand the excitement of seeing their son, but they weren’t like this when Dean came home over summer break, or any time before this.  Especially after Dean living away from home for three years now.</p>
<p>John continued to meander his way towards the porch and as he passed Sam asked, “What’s up with her?”</p>
<p>“She’s been waiting for Dean to bring someone home for three years now,”  John snorted, “Poor kid doesn’t know what’s about to hit him.”</p>
<p>‘Bring someone home’, bring who home?  Dean wasn’t dating anyone, Sam would have heard all about it if he was.</p>
<p>Sam hesitantly followed his father into the porch, he stepped into the room with enough time to watch his mother release Dean from a tight hug and all leap onto… <i>Cas</i>.</p>
<p>Bring someone home… Bring Cas home?</p>
<p>Why would his father use another romantically implication statement when he desc-</p>
<p>No.</p>
<p>There was no way.</p>
<p>Sam’s jaw was hanging limply from his face, he managed to lift his spinning head enough to see Dean and Cas’ hands.  Their hands that were holding each other.</p>
<p>“Dude,”  Dean said suddenly, “What’s up with your face?”</p>
<p>Sam looked up to see John and Cas giving him confused looks, his mom looked panicked, and Dean looked somewhere between sad and hurt.</p>
<p>“I- I didn’t know Cas was your boyfriend,”  Sam whispered, brain still running a million miles an hour.</p>
<p>“How did you not know?”  Dean asked incredulously, “Mom told you that we were and I’ve told you about all the dates we’ve been on.”</p>
<p>Sam was gaping at him.  Everything made so much more sense now, he kind of wanted to slap himself because of course Cas was Dean’s boyfriend.  </p>
<p>“I just thought you were really good friends,”  Sam defended weakly, “And I didn’t even know you liked guys, you never told me.”</p>
<p>His, oh so loving and kind, parents were both trying to suppress their laughter as the two boys faced off, and Cas was analyzing the two of them thoroughly.  </p>
<p>Dean gave Sam a face that could only be described as what-the-actual-fuck-how and said, “You pick up on literally everything.  Mom and Dad knew, everyone does, we thought that’s why you hated Michael, ‘cause I liked him and wasn’t spending time with you.”</p>
<p>Sam hung his head.  “I don’t know how I didn’t notice,”  He groaned, “And I just didn’t like that you were spending more time with him than me.”</p>
<p>Needless to say there were a lot of how-did-I-miss-that moments in Sam’s immediate future, but he was happy to say that everyone was able to laugh off his obliviousness because they realized that no one ever explicitly told Sam what was happening.  Perks of being a kid, he supposed.</p>
<p>
  <b>Bonus Scene</b>
</p>
<p>Two Christmases later saw Dean and Cas arriving back at Sam and Dean’s childhood home once again, this time with the addition of Sarah in their welcoming party.</p>
<p>After dinner and hot chocolate that night Sam, ironically, was the one to notice something was up with the two.  After some cajoling, and light begging on Mary’s part, for them to spill, the two of them revealed matching engagement rings.</p>
<p>There were smiles and some tears before Dean finally said, “So Sammy, just for the record, this means Cas is my Fiance now.”</p>
<p>Sam, despite the smiles surrounding him, glared at his brother.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>I love Oblivious Sam sooooo much, he is my child.  Also I said this is the type of fic I was going to write a lot, well that didn't happen.</p>
<p>Thank you to Van'ty for Beta-ing even though you were interrupting me while I was writing the end with whatever things about your damn sex dungeon fic you were reading.</p>
<p>I'm a complete lover of kudos and comments (seriously it's a problem) so feel free to support my addiction.</p></blockquote></div></div>
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